Thionyl Chloride → (6-Methoxy-pyridin-3-ylmethyl)-[6-(4-chloromethyl-phenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-amine

HRID 2252784Notes

Reaction equation

HRID 2252784 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([CH2:9][NH:10][C:11]2[C:12]3[CH:19]=[C:18]([C:20]4[CH:25]=[CH:24][C:23]([CH2:26]O)=[CH:22][CH:21]=4)[NH:17][C:13]=3[N:14]=[CH:15][N:16]=2)=[CH:5][CH:4]=1.O=S(Cl)[Cl:30]>C(#N)C.O1CCOCC1.CCOC(C)=O>[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([CH2:9][NH:10][C:11]2[C:12]3[CH:19]=[C:18]([C:20]4[CH:25]=[CH:24][C:23]([CH2:26][Cl:30])=[CH:22][CH:21]=4)[NH:17][C:13]=3[N:14]=[CH:15][N:16]=2)=[CH:5][CH:4]=1

Participants

6

Reactant 2

HCID 24386Thionyl ChlorideHCID 691807374-[4-(6-Methoxy-pyridin-3-ylmethylamino)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]-phenyl-methanol

Product 1

HCID 69181484(6-Methoxy-pyridin-3-ylmethyl)-[6-(4-chloromethyl-phenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-amine

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

A suspension of 3.28 g (9.1 mMol) of {4-[4-(6-methoxy-pyridin-3-ylmethylamino)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]-phenyl}-methanol in 40 ml of acetonitrile, 40 ml of dioxane and 4 ml of SOCl2 is stirred for 1 h at RT. The mixture is dissolved in EtOAc and NaHCO3-solution, the aqueous layer separated off and extracted with EtOAc. The organic layers are washed with NaHCO3-solution, water and brine, dried (Na2SO4) and partially concentrated. The crystallized title compound can be filtered off; elemental analysis for C, H and N within 0.4% of calculated value.

Workup

  1. customNaHCO3-solution, the aqueous layer separated off
  2. extractionextracted with EtOAc
  3. washThe organic layers are washed with NaHCO3-solution, water and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationpartially concentrated
  6. customThe crystallized title compound
  7. filtrationcan be filtered off

Sources & evidence

ORD record
ord-a5cc728dd69d4acb97df34ee1b072b56
Source dataset
uspto-grants-2008_01
Patent number
US07323469B2

Reaction notes

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